# Supplementary Material for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Sven Siegfried' 'Jochen Weingartner' 'Mark Nieuwenhuyzen' 'Rainer Schobert' _publ_contact_author_name 'Dr Rainer Schobert' _publ_contact_author_address ; Dr Rainer Schobert School of Chemistry The Queen's University of Belfast 32 Stranmillis Road Belfast BT9 5AG UNITED KINGDOM ; _publ_contact_author_email 'R.SCHOBERT@QUB.AC.UK' data_sieg1m _database_code_CSD 158427 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 O5' _chemical_formula_weight 268.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.456(2) _cell_length_b 8.9927(16) _cell_length_c 13.549(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.824(3) _cell_angle_gamma 90.00 _cell_volume 1377.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9547 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15084 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 31.08 _reflns_number_total 3171 _reflns_number_gt 2516 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0944P)^2^+0.0321P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3171 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1399 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.26737(12) 0.71317(16) -0.06217(13) 0.0296(3) Uani 1 1 d . . . H1A H 0.1982(18) 0.713(2) -0.1287(16) 0.039(5) Uiso 1 1 d . . . H1B H 0.3183(15) 0.6475(19) -0.0850(13) 0.030(4) Uiso 1 1 d . . . C2 C 0.31053(13) 0.87281(17) -0.03556(14) 0.0345(4) Uani 1 1 d . . . H2A H 0.2587(18) 0.937(2) -0.0189(16) 0.046(5) Uiso 1 1 d . . . H2B H 0.3172(16) 0.9122(19) -0.1048(14) 0.033(4) Uiso 1 1 d . . . C3 C 0.41877(14) 0.8801(2) 0.07358(16) 0.0400(4) Uani 1 1 d . . . H3A H 0.4394(18) 0.985(2) 0.0909(16) 0.049(5) Uiso 1 1 d . . . H3B H 0.4708(17) 0.824(2) 0.0554(15) 0.043(5) Uiso 1 1 d . . . C4 C 0.40947(13) 0.81045(18) 0.18042(14) 0.0346(4) Uani 1 1 d . . . H4A H 0.4832(17) 0.814(2) 0.2515(16) 0.046(5) Uiso 1 1 d . . . H4B H 0.3585(17) 0.868(2) 0.2038(15) 0.040(5) Uiso 1 1 d . . . C5 C 0.36676(11) 0.65076(16) 0.15441(12) 0.0273(3) Uani 1 1 d . . . H5A H 0.3602(14) 0.6068(17) 0.2235(13) 0.026(4) Uiso 1 1 d . . . H5B H 0.4151(16) 0.5903(19) 0.1346(14) 0.033(4) Uiso 1 1 d . . . C6 C 0.25884(10) 0.64301(14) 0.04473(12) 0.0237(3) Uani 1 1 d . . . O7 O 0.13731(8) 0.47012(12) -0.09561(8) 0.0283(3) Uani 1 1 d . . . H7O H 0.086(2) 0.412(3) -0.100(2) 0.065(7) Uiso 1 1 d . . . C7 C 0.20661(11) 0.48585(14) 0.02394(11) 0.0231(3) Uani 1 1 d . . . O8 O 0.28875(8) 0.37497(10) 0.06290(9) 0.0284(3) Uani 1 1 d . . . O9 O 0.22663(8) 0.23751(10) 0.05743(9) 0.0296(3) Uani 1 1 d . . . C10 C 0.20011(11) 0.23101(14) 0.15870(12) 0.0264(3) Uani 1 1 d . . . C11 C 0.14452(10) 0.37407(14) 0.16893(11) 0.0236(3) Uani 1 1 d . . . C12 C 0.14720(10) 0.48854(14) 0.10190(11) 0.0228(3) Uani 1 1 d . . . O13 O 0.05032(8) 0.69996(11) 0.13533(9) 0.0298(3) Uani 1 1 d . . . C13 C 0.11718(10) 0.64508(14) 0.10604(11) 0.0231(3) Uani 1 1 d . . . O14 O 0.17767(8) 0.73160(10) 0.06797(8) 0.0275(3) Uani 1 1 d . . . C15 C 0.12216(13) 0.09887(17) 0.12675(15) 0.0329(3) Uani 1 1 d . . . H15A H 0.1030(18) 0.076(2) 0.1934(17) 0.049(5) Uiso 1 1 d . . . H15B H 0.1599(19) 0.009(2) 0.1128(16) 0.049(5) Uiso 1 1 d . . . H15C H 0.0610(18) 0.124(2) 0.0555(16) 0.042(5) Uiso 1 1 d . . . C16 C 0.30336(13) 0.20537(18) 0.27175(14) 0.0333(4) Uani 1 1 d . . . H16A H 0.3513(17) 0.290(2) 0.2882(15) 0.039(5) Uiso 1 1 d . . . H16B H 0.3367(18) 0.122(2) 0.2597(16) 0.046(5) Uiso 1 1 d . . . H16C H 0.2839(18) 0.187(2) 0.3384(18) 0.051(5) Uiso 1 1 d . . . C17 C 0.09622(12) 0.37843(17) 0.25686(13) 0.0285(3) Uani 1 1 d . . . H17A H 0.0821(14) 0.4807(18) 0.2744(13) 0.025(4) Uiso 1 1 d . . . H17B H 0.1422(15) 0.328(2) 0.3276(14) 0.031(4) Uiso 1 1 d . . . H17C H 0.0286(17) 0.329(2) 0.2242(15) 0.041(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0207(6) 0.0332(8) 0.0346(9) 0.0044(6) 0.0115(6) -0.0015(5) C2 0.0277(7) 0.0321(8) 0.0459(10) 0.0100(7) 0.0176(7) -0.0023(6) C3 0.0257(7) 0.0366(9) 0.0565(11) 0.0038(7) 0.0162(7) -0.0089(6) C4 0.0225(6) 0.0335(8) 0.0441(10) -0.0026(7) 0.0104(6) -0.0061(6) C5 0.0182(6) 0.0290(7) 0.0339(8) 0.0014(6) 0.0101(5) -0.0011(5) C6 0.0164(5) 0.0233(6) 0.0341(8) 0.0009(5) 0.0131(5) 0.0021(4) O7 0.0210(4) 0.0320(5) 0.0321(6) -0.0032(4) 0.0112(4) -0.0048(4) C7 0.0181(5) 0.0224(6) 0.0296(7) 0.0000(5) 0.0109(5) 0.0008(5) O8 0.0193(4) 0.0219(5) 0.0474(6) 0.0013(4) 0.0173(4) 0.0009(3) O9 0.0275(5) 0.0202(5) 0.0456(7) -0.0033(4) 0.0197(5) -0.0026(4) C10 0.0217(6) 0.0234(6) 0.0357(8) 0.0006(5) 0.0135(6) -0.0002(5) C11 0.0147(5) 0.0235(6) 0.0305(7) -0.0026(5) 0.0075(5) -0.0026(4) C12 0.0145(5) 0.0237(6) 0.0299(7) -0.0023(5) 0.0090(5) -0.0012(4) O13 0.0185(4) 0.0272(5) 0.0469(7) -0.0038(4) 0.0169(4) 0.0002(4) C13 0.0165(5) 0.0234(6) 0.0295(7) -0.0014(5) 0.0097(5) -0.0020(4) O14 0.0176(4) 0.0228(5) 0.0457(6) 0.0018(4) 0.0168(4) 0.0016(3) C15 0.0301(7) 0.0244(7) 0.0434(9) -0.0012(6) 0.0146(7) -0.0052(6) C16 0.0234(6) 0.0299(8) 0.0427(10) 0.0038(7) 0.0100(6) 0.0032(6) C17 0.0219(6) 0.0312(8) 0.0351(9) 0.0024(6) 0.0146(6) -0.0005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.522(2) . ? C1 C6 1.624(2) . ? C2 C3 1.528(2) . ? C3 C4 1.625(3) . ? C4 C5 1.521(2) . ? C5 C6 1.5307(18) . ? C6 O14 1.4225(15) . ? C6 C7 1.5318(18) . ? O7 C7 1.4883(17) . ? C7 O8 1.3661(15) . ? C7 C12 1.5232(19) . ? O8 O9 1.4437(13) . ? O9 C10 1.5415(18) . ? C10 C15 1.4796(19) . ? C10 C11 1.4948(18) . ? C10 C16 1.549(2) . ? C11 C12 1.3824(19) . ? C11 C17 1.544(2) . ? C12 C13 1.4636(18) . ? O13 C13 1.1714(16) . ? C13 O14 1.3288(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 107.70(13) . . ? C1 C2 C3 110.48(13) . . ? C2 C3 C4 118.78(12) . . ? C5 C4 C3 107.83(13) . . ? C4 C5 C6 110.32(11) . . ? O14 C6 C5 100.12(11) . . ? O14 C6 C7 105.72(9) . . ? C5 C6 C7 110.65(11) . . ? O14 C6 C1 107.38(10) . . ? C5 C6 C1 119.25(10) . . ? C7 C6 C1 112.11(11) . . ? O8 C7 O7 110.44(10) . . ? O8 C7 C12 104.29(11) . . ? O7 C7 C12 121.84(10) . . ? O8 C7 C6 114.27(10) . . ? O7 C7 C6 107.17(10) . . ? C12 C7 C6 98.65(10) . . ? C7 O8 O9 107.86(9) . . ? O8 O9 C10 107.30(9) . . ? C15 C10 C11 116.47(11) . . ? C15 C10 O9 97.44(12) . . ? C11 C10 O9 109.31(11) . . ? C15 C10 C16 109.89(12) . . ? C11 C10 C16 105.13(12) . . ? O9 C10 C16 119.12(11) . . ? C12 C11 C10 116.11(12) . . ? C12 C11 C17 127.78(12) . . ? C10 C11 C17 116.04(11) . . ? C11 C12 C13 127.88(13) . . ? C11 C12 C7 126.62(11) . . ? C13 C12 C7 104.37(11) . . ? O13 C13 O14 118.98(12) . . ? O13 C13 C12 130.36(12) . . ? O14 C13 C12 110.65(11) . . ? C13 O14 C6 109.24(10) . . ? _diffrn_measured_fraction_theta_max 0.717 _diffrn_reflns_theta_full 31.08 _diffrn_measured_fraction_theta_full 0.717 _refine_diff_density_max 0.452 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.066 data_ss7ringm _database_code_CSD 158428 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 O5' _chemical_formula_weight 282.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.348(2) _cell_length_b 8.8063(9) _cell_length_c 18.3387(18) _cell_angle_alpha 90.00 _cell_angle_beta 121.243(2) _cell_angle_gamma 90.00 _cell_volume 2809.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Thin needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8041 _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_sigmaI/netI 0.0774 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.75 _reflns_number_total 3090 _reflns_number_gt 2082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3090 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 0.845 _refine_ls_restrained_S_all 0.845 _refine_ls_shift/su_max 0.094 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.18739(11) 0.6055(2) 0.42710(13) 0.0253(4) Uani 1 1 d . . . H1A H 0.2177(11) 0.564(2) 0.4842(13) 0.025(5) Uiso 1 1 d . . . H1B H 0.2182(11) 0.685(2) 0.4197(12) 0.029(5) Uiso 1 1 d . . . C2 C 0.11278(11) 0.6758(2) 0.41246(14) 0.0302(4) Uani 1 1 d . . . H2A H 0.1252(12) 0.782(3) 0.4363(13) 0.043(6) Uiso 1 1 d . . . H2B H 0.0783(11) 0.685(2) 0.3516(14) 0.030(5) Uiso 1 1 d . . . C3 C 0.07509(12) 0.5947(2) 0.45530(14) 0.0326(5) Uani 1 1 d . . . H3A H 0.1016(12) 0.628(2) 0.5168(14) 0.037(6) Uiso 1 1 d . . . H3B H 0.0201(13) 0.625(2) 0.4244(14) 0.040(6) Uiso 1 1 d . . . C4 C 0.07795(13) 0.4217(2) 0.45527(13) 0.0315(5) Uani 1 1 d . . . H4A H 0.0378(13) 0.384(2) 0.4663(14) 0.044(6) Uiso 1 1 d . . . H4B H 0.1302(13) 0.383(2) 0.5045(14) 0.039(6) Uiso 1 1 d . . . C5 C 0.06579(12) 0.3495(2) 0.37338(13) 0.0329(5) Uani 1 1 d . . . H5A H 0.0473(12) 0.245(3) 0.3690(14) 0.046(6) Uiso 1 1 d . . . H5B H 0.0257(13) 0.402(2) 0.3197(15) 0.043(6) Uiso 1 1 d . . . C6 C 0.13944(12) 0.3323(2) 0.37155(13) 0.0288(4) Uani 1 1 d . . . H6A H 0.1315(11) 0.271(2) 0.3246(14) 0.042(6) Uiso 1 1 d . . . H6B H 0.1774(11) 0.284(2) 0.4240(14) 0.031(5) Uiso 1 1 d . . . C7 C 0.17645(10) 0.47884(18) 0.36438(11) 0.0227(4) Uani 1 1 d . . . O8 O 0.12932(7) 0.53718(13) 0.27824(8) 0.0259(3) Uani 1 1 d . . . C9 C 0.16984(10) 0.53217(18) 0.23822(11) 0.0231(4) Uani 1 1 d . . . O9 O 0.13957(7) 0.57574(14) 0.16459(8) 0.0294(3) Uani 1 1 d . . . C10 C 0.24711(10) 0.47286(18) 0.29489(11) 0.0221(4) Uani 1 1 d . . . C11 C 0.25083(10) 0.44425(18) 0.36977(11) 0.0233(4) Uani 1 1 d . . . O11 O 0.30738(8) 0.39428(15) 0.44394(8) 0.0308(3) Uani 1 1 d . . . H110 H 0.3512(16) 0.376(3) 0.4383(17) 0.071(9) Uiso 1 1 d . . . C12 C 0.30483(10) 0.45777(17) 0.26872(11) 0.0233(4) Uani 1 1 d . . . C13 C 0.28264(13) 0.4409(2) 0.18738(14) 0.0340(5) Uani 1 1 d . . . H13A H 0.2300(14) 0.435(2) 0.1442(15) 0.041(6) Uiso 1 1 d . . . H13B H 0.3204(13) 0.437(2) 0.1685(13) 0.039(6) Uiso 1 1 d . . . C14 C 0.38998(10) 0.46932(19) 0.33882(12) 0.0251(4) Uani 1 1 d . . . O14 O 0.40734(7) 0.35461(14) 0.40393(8) 0.0262(3) Uani 1 1 d . . . H14O H 0.3968(14) 0.256(3) 0.3792(17) 0.067(8) Uiso 1 1 d . . . C15 C 0.40605(12) 0.6213(2) 0.38501(14) 0.0314(4) Uani 1 1 d . . . H15A H 0.4583(13) 0.626(2) 0.4328(14) 0.037(6) Uiso 1 1 d . . . H15B H 0.3694(12) 0.638(2) 0.4053(13) 0.034(5) Uiso 1 1 d . . . H15C H 0.3987(11) 0.709(2) 0.3453(13) 0.036(5) Uiso 1 1 d . . . C16 C 0.44471(12) 0.4439(2) 0.30720(14) 0.0323(5) Uani 1 1 d . . . H16A H 0.4991(14) 0.446(2) 0.3584(15) 0.041(6) Uiso 1 1 d . . . H16B H 0.4375(12) 0.525(2) 0.2658(14) 0.036(6) Uiso 1 1 d . . . H16C H 0.4355(12) 0.348(3) 0.2780(13) 0.038(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0242(10) 0.0264(8) 0.0273(10) -0.0027(7) 0.0147(9) -0.0013(7) C2 0.0325(11) 0.0294(9) 0.0309(11) 0.0018(8) 0.0180(10) 0.0063(7) C3 0.0314(11) 0.0389(10) 0.0317(12) 0.0014(8) 0.0194(10) 0.0066(8) C4 0.0343(12) 0.0385(10) 0.0282(11) -0.0013(8) 0.0209(10) -0.0035(8) C5 0.0340(11) 0.0403(10) 0.0295(11) -0.0084(8) 0.0200(10) -0.0108(9) C6 0.0374(11) 0.0261(9) 0.0286(11) -0.0032(8) 0.0211(10) -0.0050(8) C7 0.0231(9) 0.0271(8) 0.0177(9) 0.0014(6) 0.0104(8) 0.0004(7) O8 0.0215(7) 0.0360(7) 0.0210(7) 0.0029(5) 0.0115(6) 0.0037(5) C9 0.0254(9) 0.0235(8) 0.0223(9) -0.0021(7) 0.0138(8) -0.0015(6) O9 0.0311(7) 0.0361(7) 0.0197(7) 0.0038(5) 0.0122(6) 0.0070(5) C10 0.0214(9) 0.0248(8) 0.0187(9) -0.0010(6) 0.0093(8) -0.0009(6) C11 0.0232(9) 0.0239(8) 0.0211(9) 0.0004(6) 0.0104(8) 0.0017(6) O11 0.0271(7) 0.0433(7) 0.0219(7) 0.0084(5) 0.0127(6) 0.0115(6) C12 0.0253(9) 0.0218(8) 0.0252(10) -0.0006(7) 0.0148(8) 0.0010(6) C13 0.0303(12) 0.0475(11) 0.0277(11) -0.0028(8) 0.0175(10) 0.0022(8) C14 0.0230(9) 0.0265(8) 0.0274(10) -0.0008(7) 0.0141(8) 0.0001(7) O14 0.0260(7) 0.0275(6) 0.0243(7) 0.0004(5) 0.0124(6) 0.0030(5) C15 0.0274(11) 0.0288(9) 0.0368(12) -0.0071(8) 0.0157(10) -0.0036(7) C16 0.0276(11) 0.0365(11) 0.0370(12) 0.0009(9) 0.0197(11) 0.0034(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.529(3) . ? C1 C7 1.533(2) . ? C2 C3 1.530(3) . ? C3 C4 1.525(3) . ? C4 C5 1.528(3) . ? C5 C6 1.524(3) . ? C6 C7 1.534(2) . ? C7 O8 1.452(2) . ? C7 C11 1.496(2) . ? O8 C9 1.359(2) . ? C9 O9 1.220(2) . ? C9 C10 1.459(2) . ? C10 C11 1.359(2) . ? C10 C12 1.487(2) . ? C11 O11 1.321(2) . ? C12 C13 1.324(3) . ? C12 C14 1.534(3) . ? C14 O14 1.461(2) . ? C14 C16 1.515(3) . ? C14 C15 1.526(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C7 114.73(15) . . ? C1 C2 C3 115.92(16) . . ? C4 C3 C2 115.93(16) . . ? C3 C4 C5 115.41(17) . . ? C6 C5 C4 113.78(17) . . ? C5 C6 C7 116.78(16) . . ? O8 C7 C11 102.63(13) . . ? O8 C7 C1 108.40(13) . . ? C11 C7 C1 110.51(14) . . ? O8 C7 C6 108.32(14) . . ? C11 C7 C6 110.36(14) . . ? C1 C7 C6 115.75(15) . . ? C9 O8 C7 109.43(13) . . ? O9 C9 O8 119.22(16) . . ? O9 C9 C10 129.79(17) . . ? O8 C9 C10 110.99(15) . . ? C11 C10 C9 105.12(15) . . ? C11 C10 C12 132.06(16) . . ? C9 C10 C12 122.79(16) . . ? O11 C11 C10 131.66(17) . . ? O11 C11 C7 116.55(15) . . ? C10 C11 C7 111.79(15) . . ? C13 C12 C10 120.59(17) . . ? C13 C12 C14 121.89(17) . . ? C10 C12 C14 117.47(15) . . ? O14 C14 C16 107.25(14) . . ? O14 C14 C15 105.16(15) . . ? C16 C14 C15 110.71(16) . . ? O14 C14 C12 109.16(14) . . ? C16 C14 C12 113.84(16) . . ? C15 C14 C12 110.30(15) . . ? _diffrn_measured_fraction_theta_max 0.848 _diffrn_reflns_theta_full 28.75 _diffrn_measured_fraction_theta_full 0.848 _refine_diff_density_max 0.284 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.069